Was this a groovy deal or what?! Here I was, moored stern-to for the evening, hard by the offices of Southwest Florida Yachts, a charter outfit specializing in Grand Banks trawlers and other passagemaking vessels. Sitting in the cockpit of what was to be my home for the next four days, a Grand Banks 32 Sedan called Patience. In a battered deck chair. Watching the stars tumble out over Fort Myers. I inhaled the aroma of fried seafood emanating from Hurricane Harry’s Waterfront Bar & Grill across the way, propped my bare feet up on Patience’s taffrail, slouched even further into my chair, and thought about the days ahead as a tiki-bar guy sang, “Yes, I am a pirate, two-hundred years too late…”

The weather looked fair. Northerly winds were forecast at 20 knots or so, but there was no rain predicted, and maybe some sun. Not bad for 100 miles or so of voyaging the mangrove-fringed waterways of southwestern Florida, amid a wind-thwarting array of barrier islands: Sanibel, Captiva, North Captiva, and Cayo Costa.

There were worrisome details, though. Like the fact that Patience had been repowered with a single four-cylinder 90-hp Ford Lehman diesel, a form of propulsion famed for sippin’ fuel but seldom praised for dockside maneuvering prowess under windy conditions, especially with no bow thruster. Would I be able to handle Patience over the next few days without making a total doofus of myself?

Then there was the fact that my only companion would be a boating neophyte, photographer Jeffrey Salter. Would he be able to learn the ropes—literally—and somehow transform himself into an able deckhand and good shipmate? Would he even want to try?

And finally there was the fact that the story I was trying to do had a problematic side. Granted, the main point made sense: Prior to venturing into the realm of passagemaking and spending a pile of money on a boat, I figured buyers should actually charter the sort of vessels they fancied and spend a few days seeing if those vessels genuinely fit their mindset and lifestyle. But there was one glitch: I was on the verge of buying a passagemaker myself, perhaps even a slow-mo boat like Patience. Was I really the easy-going, slo-mo-lovin’ guy I thought I was? Or was there some potential for disillusionment here?